HCID 18633467, compound → HCID 18633448, compound

HRID 232378Notes

Reaction equation

HRID 232378 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][C@@H:7]([N:17]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:6]1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][C@@H:7]([N:17]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 18633467HCID 18633467, compound

Product 1

HCID 18633448HCID 18633448, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7.3 g of trans-3'-O-acetyl-2',5'-dideoxy-5'-(ethoxycarbonylmethylene)-5-ethyluridine in 150 ml of ethanol was hydrogenated over 0.5 g of 10% palladium-on-carbon catalyst for 6 hours. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was recrystallized from ethanol to give 5.8 g of 3'-O-acetyl-2',5'-dideoxy-5'-(ethoxycarbonylmethyl)-5-ethyluridine in the form of a white solid of melting point 137°-138° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-239c6ec95a7947e1b64ee41cb0caff39
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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